President Donald Trump signed a series of executive orders Monday that aim to roll back cashless bail policies in Washington, D.C., and other American cities. The orders mark one of Trump’s most direct efforts to reshape criminal justice policies in the nation’s capital while sending a strong message to jurisdictions nationwide.

According to documents released by the White House, the first executive order focuses specifically on Washington, D.C. The order warns city officials that if the District does not reverse its cashless bail system, the federal government could respond by reconsidering federal funding, services, and approvals tied to the city.

The directive also allows for Attorney General Pam Bondi to play a role, though the fact sheet did not clarify what legal or enforcement measures she might take.

The second executive order extends to cities across the nation that currently use cashless bail. It instructs federal agencies to identify government funds that could be “suspended or terminated” for states or localities that continue to release defendants without requiring money bail.

Another significant detail in the order is that law enforcement is asked to ensure that individuals arrested in D.C. are taken into federal custody whenever possible under existing law. Critics argue this could shift significant legal power away from local authorities and into the hands of federal agencies, altering how criminal cases are handled in the District.

A spokesperson for Mayor Muriel Bowser’s office declined to comment on the administration’s move.

This executive action comes on the heels of Trump’s decision to arm National Guard troops in Washington, D.C., a move intended to combat rising crime in the city. The president has consistently argued that cash bail reform policies create dangers for communities, pointing to reoffending as a major issue.

In a recent statement, Trump described cashless bail as a “disaster,” claiming it has caused “problems we never had before.” Supporters of the orders say the president is prioritizing public safety, victims’ rights, and law enforcement accountability.

On the other hand, critics say the executive orders represent federal overreach into local decision-making. They also note that cash bail disproportionately impacts low-income defendants, many of whom are unable to pay for release even when they pose no danger to the public.

Washington, D.C. has operated under a cashless bail system since 1992, making it one of the earliest jurisdictions to adopt the policy. Judges currently decide whether a defendant poses a danger to others or is a flight risk before trial. If deemed a risk, the defendant is held in detention. If not, they can be released without posting bail.

Supporters of cashless bail argue that the system prevents wealth from determining who sits in jail while awaiting trial. They point to research showing that many low-level offenders fail to appear in court due to poverty, not criminal intent.

Opponents, including Trump and allies like U.S. Attorney Jeanine Pirro, claim that the policy has led to repeat offenses and unsafe streets. On Fox News, Pirro argued that “cashless bail is when all of the problems started,” emphasizing that too many defendants are released and then “reoffending again.”

States like Illinois, New Mexico, and New Jersey have already eliminated or significantly reduced cash bail, and the debate continues to play out across the country.

Alongside the bail orders, Trump signed another executive directive targeting flag desecration. The order instructs Attorney General Bondi to “vigorously prosecute” individuals who damage or burn the American flag and to pursue legal challenges regarding the scope of the First Amendment in such cases.

Non-citizens who desecrate the flag could also face revoked visas, canceled residency permits, or deportation proceedings, according to the White House fact sheet. Legal experts note, however, that the Supreme Court’s 1989 decision in Texas v. Johnson protects flag burning as free speech, meaning the executive order will likely face constitutional challenges.

Trump’s focus on reshaping Washington, D.C. sets him apart from previous presidents. His administration has recently:

The combination of these moves has sparked debate over how much control a president should exert over the nation’s capital and whether Trump’s efforts amount to an unprecedented federal takeover of D.C. governance.

With the executive orders signed, the legal and political battles over cashless bail reform in America are far from over. Supporters of reform argue that eliminating bail keeps the system fair, while opponents insist that cashless bail leads to higher crime rates, unsafe neighborhoods, and repeat offenders.

As National Guard troops now patrol D.C. with firearms and Trump threatens to expand deployments to cities like Baltimore, Chicago, and New York, the clash over criminal justice reform, public safety, and federal authority will likely intensify in the months ahead.

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